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[ CAS No. 22123-14-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 22123-14-4
Chemical Structure| 22123-14-4
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Quality Control of [ 22123-14-4 ]

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Product Details of [ 22123-14-4 ]

CAS No. :22123-14-4 MDL No. :MFCD00052900
Formula : C7H5ClF3N Boiling Point : No data available
Linear Structure Formula :- InChI Key :SXLBWNSGCIEART-UHFFFAOYSA-N
M.W : 195.57 Pubchem ID :2736626
Synonyms :

Calculated chemistry of [ 22123-14-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.21
TPSA : 12.89 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 4.21
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 3.44
Consensus Log Po/w : 3.06

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.31
Solubility : 0.0959 mg/ml ; 0.00049 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.179 mg/ml ; 0.000915 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.92
Solubility : 0.0236 mg/ml ; 0.000121 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 22123-14-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22123-14-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 22123-14-4 ]

[ 22123-14-4 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 22123-14-4 ]
  • [ 862120-75-0 ]
YieldReaction ConditionsOperation in experiment
70% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h;Heating / reflux; 2-(bromomethyl)-6-chloro-4-(trifluoromethyl)pyridine. (<strong>[22123-14-4]2-chloro-6-methyl-4-(trifluoromethyl)pyridine</strong> (10.0 g, 51 mmol), N-bromosuccinimide (10.9 g, 61 mmol), and 2,2'-azobis(2-methylpropionitrile) (164mg, 1 mmol) were combined in carbon tetrachloride (200 mL) and heated to reflux. After 16 h, the reaction mixture was cooled to 0 C. and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (100% hexanes) to produce 9.1 g (70%) as a light yellow oil. 1H-NMR (CDCl3, 400 MHz) delta7.59 (s, 1H), 7.47 (s, 1H), 4.52 (s, 2H).
70% With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h;Reflux; (2-chloro-6-methyl-4- (trifluoromethyl)pyridine (10.0 g, 51 mmol), N-bromosuccinimide (10.9 g, 61 mmol), and 2,2'-azobis(2-methylpropionitrile) (164mg, 1 mmol) were combined in carbon tetrachloride (200 mL) and heated to reflux. After 16 h, the reaction mixture was cooled to 0C and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (100% hexanes) to produce 9.1 g (70%) as a light yellow oil. 1H-NMR (CDCl3, 400 MHz) delta 7.59 (s, IH), 7.47 (s, IH), 4.52 (s, 2H).
  • 2
  • [ 22123-14-4 ]
  • [ 1004794-10-8 ]
YieldReaction ConditionsOperation in experiment
51% With selenium(IV) oxide; In 1,2-dichloro-benzene; at 180℃; for 3h; 6-hydroxy-4-(trifluoromethyl)picolinaldehyde. <strong>[22123-14-4]2-chloro-6-methyl-4-(trifluoromethyl)pyridine</strong> (2.0 g, 10.2 mmol) and selenium dioxide (3.5 g, 30.6 mmol) were dissolved in dichlorobenzene (40 ml) and heated to 180 C. and mixed for 3 hours. The reaction mixture was allowed to cool to room temperature. The precipitate was removed via vacuum filtration. Column chromatography on silica gel (10% -70% ethyl acetate/hexanes) afforded 1.00 g desired product (51%) 1HNMR (CDCl3 400MHz) delta9.58 (s, 1H), 7.13 (s, 1H), 6.87 (s, 1H).
51% With selenium(IV) oxide; In 1,2-dichloro-benzene; at 180℃; for 3h; 2-chloro-6-methyl-4- (trifluoromethyl)pyridine (2.0 g, 10.2 mmol) and selenium dioxide (3.5 g, 30.6 mmol) were dissolved in dichlorobenzene (40 ml) and heated to 1800C and mixed for 3 hours. The reaction mixture was allowed to cool to room temperature. The precipitate was removed via vacuum filtration. Column chromatography on silica gel (10% - 70% ethyl acetate / hexanes) afforded 1.00 g desired product (51%) 1HNMR (CDCl3 400MHz) delta 9.58 (s, IH), 7.13 (s, IH), 6.87 (s, IH).
  • 3
  • [ 110-85-0 ]
  • [ 22123-14-4 ]
  • [ 872592-72-8 ]
YieldReaction ConditionsOperation in experiment
70.2% With triethylamine; In 1,4-dioxane; at 100℃; for 5h; A solution of <strong>[22123-14-4]2-chloro-6-methyl-4-(trifluoromethyl)pyridine</strong> (1.0 g, 5.11 mmol), piperazine (1.32 g, 15.3 mmol), and triethylamine (0.71 mL, 5.1 mmol) were mixed in 1,4-dioxane (10 mL). After stirring at 100 C. for 5 h, the reaction solution was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (10% MeOH/5% Et3N/EtOAc) to yield the desired product (880 mg, 70.2%). LCMS calculated for C11H15F3N3: (M+1) 246.1; found 246.1.
YieldReaction ConditionsOperation in experiment
The following may be mentioned as examples of pyridine derivatives of the formula (IV): ... 2-chloro-4,6-dimethyl-pyridine 2-fluoro-4,6-dimethyl-pyridine 2-chloro-6-methyl-4-propyl-pyridine 2-chloro-6-methyl-4-isopropyl-pyridine 2-chloro-6-methyl-4-trifluoromethyl-pyridine 2,3-dichloro-4,6-dimethyl-pyridine 2-chloro-5-fluoro-4,6-dimethyl-pyridine 2-chloro-3-cyano-4,6-dimethyl-pyridine ...
  • 5
  • [ 22123-14-4 ]
  • 2-(2-dimethylaminoethylamino)-4-trifluoromethyl-6-methylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
A. 2-(2-Dimethylaminoethylamino)-4-trifluoromethyl-6-methylpyridine The title compound is obtained by following the procedure of Example 38, Part A except substituting <strong>[22123-14-4]2-chloro-4-trifluoromethyl-6-methylpyridine</strong> for 2,6-dichloropyridine.
  • 6
  • [ 22123-14-4 ]
  • [ 862120-75-0 ]
  • [ 1089330-99-3 ]
YieldReaction ConditionsOperation in experiment
44% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 3h;Heating / reflux; Procedure B; Step A; A solution of 2-chloro-6-methyl-4-trifluoromethyl pyridine (21.18 g, 108.3 mmol, Maybridge CD 10452), N-bromosuccinimide (21.20 g, 119.2 mmol, Aldrich) in tetrachloromethane (200 mL) was stirred at gentle reflux while a solution of 2,2'-azobisisobutyronitrile (1.87 mL) in tetrachloromethane (50 mL) was added, drop wise. Heating was continued for three hours, after which time the reaction mixture was allowed to cool to room temperature, washed with water (4×100 mL), dried with anhydrous magnesium sulfate and evaporated to dryness. The crude product (34 g) was purified on a Silica gel column using ethyl acetate/hexane mixture with the concentration of ethyl acetate gradually rising from 0% to 5% at the end of the separation. In this manner it was obtained: 9.6 g of 2-(alpha,alpha-dibromomethyl)-6-chloro-4-trifluoromethyl pyridine, 13.1 g of the desired 2-(alpha-bromomethyl)-6-chloro-4-trifluoromethyl pyridine (44%) and 9.03 g of unreacted starting material. 2-(alpha,alpha-Dibromomethyl)-6-chloro-4-trifluoromethyl pyridine: 1H NMR (500 MHz, CDCl3): 7.95 (s, 1H), 7.53 (s, 1H), 6.62 (s, 1H). 2-(alpha-Bromomethyl)-6-chloro-4-trifluoromethyl pyridine: 1H NMR (500 MHz, CDCl3): 7.62 (s, 1H), 7.51 (s, 1H), 4.55 (s, 2H).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 90℃; To a solution of <strong>[22123-14-4]2-chloro-6-methyl-4-(trifluoromethyl)pyridine</strong> (1.514 ml, 10.2 mmol) in CC14 (30 ml) was added BS (2730 mg, 15.3 mmol) and AIBN (168 mg, 1.02 mmol) and the resulting mixture was stirred at 90 C overnight, then filtered and the solution was evaporated and purified via silica gel chromatography (0 - 10 % EtOAc in hexanes to give a mixture of 2-chloro-6- methyl-4-(trifluoromethyl)pyridine, 2-(bromomethyl)-6-chloro-4-(trifluoromethyl)pyridine and 2-chloro-6-(dibromomethyl)-4-(trifluoromethyl)pyridine (1812 mg, 3.30 mmol, 32% yield, -50% monobromo) as an orange liquid. MS (ES+) C7H4BrClF3N requires: 274, found: 274, 276 [M+H]+.
  • 7
  • [ 22123-14-4 ]
  • [ 823222-00-0 ]
YieldReaction ConditionsOperation in experiment
67% With tetra-n-butylammonium permanganate; In pyridine; at 80℃; for 3h; To a solution of 300 mg of <strong>[22123-14-4]2-chloro-6-methyl-4-(trifluoromethyl)-pyridine</strong> (1.49 mmol) in pyridine (5 ml) was added a solution of 1.61 g of tetrabutylammonium permanganate (4.46 mmol) in pyridine (4.5 ml) and the reaction mixture was stirred at 80 C. for 3 h. The reaction mixture was then poured into a mixture of water and ice and then NaHSO3 solution (40% in water) was added until the color turned light yellow. The mixture was then acidified by addition of 2N HCl and extracted with ethyl acetate. The combined organic layers were then washed with 1N HCl and brine, dried (Na2SO4), filtered and concentrated. The remaining residue was purified by chromatography (DCM/MeOH 100:0 to 90:10) to yield 224 mg (67%) of a gray liquid. MS (ISP) 224.3 (M-H)-.
  • 8
  • [ 22123-14-4 ]
  • [ 22123-09-7 ]
YieldReaction ConditionsOperation in experiment
With hydrazine; In ethanol;Heating / reflux; One equivalent of <strong>[22123-14-4]2-chloro-4-(trifluoromethyl)-6-methylpyridine</strong> (13) and 1.5 equivalent of hydrazine hydrate were mixed in ethanol. The solution turned yellow after being stirred for several minutes. The reaction mixture was refluxed until TLC analysis showed no starting material left. The solvent was then removed under vacuum, and the resulting slurry was extracted with ether three times. The combined ether solution was dried over anhydrous MgSO4 and evaporated to afford the crude product, which was then re-crystallized from ethanol to give compound 14.
  • 9
  • [ 22123-14-4 ]
  • [ 114715-38-7 ]
  • [ 952444-06-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In diethylene glycol; at 140℃; for 2h;microwave reaction; Reference Example 29: Synthesis of (S)-N-(1-benzylpyrrolidin-3-yl)-6-methyl-4-trifluoromethylpyridin-2-amine A mixture of <strong>[22123-14-4]2-chloro-6-methyl-4-trifluoromethylpyridine</strong> (0.196 g), (S)-1-benzyl-3-aminopyrrolidine (0.529 g), diethylene glycol (4 mL), and N,N-diisopropylethylamine (0.52 mL) was heated at 140C for 2 h using a microwave reaction apparatus. After completion of the reaction, water and ethyl acetate were added to the reaction solution, the mixture was extracted with ethyl acetate, washed with saturated brine, and then dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, and then the crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (silica gel, hexane/ethyl acetate = 5:1-2:1) to obtain (S)-N-(1-benzylpyrrolidin-3-yl)-6-methyl-4-trifluoromethylpyridin-2-amine (0.082 g). 1H-NMR (300 MHz, DMSO-d6): delta7.20-7.34 (m, 5H), 6.60 (s, 1H), 6.32 (s, 1H), 5.01 (d, J=8.00 Hz, 1H), 4.20-4.30 (m, 1H), 3.63 (d, J=5.8 Hz, 2H), 2.75-2.85 (m, 2H), 2.50-2.60 (m, 1H), 2.40 (s, 3H), 2.30-2.50 (m, 2H), 1.60-1.70 (m, 1H)
  • 10
  • [ 22123-14-4 ]
  • [ 165385-89-7 ]
YieldReaction ConditionsOperation in experiment
With ammonia; at 120℃; for 24h; A mixture of 4.7 g <strong>[22123-14-4]2-chloro-6-methyl-4-trifluoromethyl-pyridine</strong> and 80 g ammonia was heated in an autoclave at 120 C. for 24 h. Ammonia was allowed to evaporate and the residue was purified on silica gel with methylene chloride:methanol:ammonia=9:1:0.1 to yield 4.01 g of the title compound as off white crystals MS (ISP) M+H+=177.1 melting at 53.5-54.5 C.
  • 11
  • [ 22123-14-4 ]
  • [ 557-21-1 ]
  • [ 451459-19-1 ]
YieldReaction ConditionsOperation in experiment
tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 90℃; for 10h; <Reference Production Example 20>To 10 ml of N,N-dimethylformamide were added 1 g of 2-chloro-6-methyl-4- trifluoromethylpyridine, 1.2 g of zinc cyanide and 0.24 g of tetrakistriphenylphosphinepalladium, and the mixture was stirred at 900C for 10 hours.After allowing to cool, the reaction solution was poured into water, and the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated.The residue was subjected to silica gel column chromatography to obtain 0.8 g of 6- methyl-4-trifluoromethylpyridine-2-carbonitrile.6-Methyl-4-trifluoromethylpyridine-2-carbonitrile1H-NMR: 2.72 (s, 3H), 7.60 (s, IH), 7.72 (s, IH)
  • 12
  • [ 22123-14-4 ]
  • [ 278597-30-1 ]
  • [ 1245613-57-3 ]
  • 13
  • [ 22123-14-4 ]
  • [ 1158787-97-3 ]
  • 14
  • [ 676-58-4 ]
  • [ 39890-98-7 ]
  • [ 22123-14-4 ]
YieldReaction ConditionsOperation in experiment
61% iron(III) chloride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; Synthesis Example 2 In the same manner as in Synthesis Example 1, except for using 4.65 g (0.0215 mol) of 2,6-dichloro-4-trifluoromethylpyridine and using 7.5 mL of a tetrahydrofuran solution of 3.0 mol/L of methylmagnesium chloride (containing 0.0226 mol of MeMgCl) as the Grignard reagent, 2.67 g (purity: 95.3%, yield: 61%) of 2-chloro-6-methyl-4-trifluoromethylpyridine was obtained.
  • 15
  • [ 75-16-1 ]
  • [ 39890-98-7 ]
  • [ 22123-14-4 ]
YieldReaction ConditionsOperation in experiment
73% iron(II) chloride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;Product distribution / selectivity; Synthesis Example 3 In the same manner as in Synthesis Example 1, except for using 4.61 g (0.0213 mol) of 2,6-dichloro-4-trifluoromethylpyridine and using 15 mg of iron(II) chloride as a metal catalyst, 3.16 g (purity: 96.6%, yield: 73%) of 2-chloro-6-methyl-4-trifluoromethylpyridine was obtained.
62.4% With iron(III) chloride; In tetrahydrofuran; at 0 - 25℃; for 2h;Inert atmosphere; The 2,6-dichloro-4 - (trifluoromethyl) pyridine (10.8g, 50mmol) dissolved in tetrahydrofuran (100 ml) in, adding anhydrous ferric trichloride (0.811g, 5mmol), under the protection of nitrogen, 0 C lower dropwise methyl bromide of magnesium oxide (1mol/L ether solution, 50 ml, 50mmol), the temperature is increased to 25 C stirring 2 hours, water (100 ml), ethyl acetate extraction (150 ml × 2), combined organic phase, dried anhydrous sodium sulfate, concentrated under vacuum, to get the yellow oily title compound (6.1g, yield 62.4%).
  • 16
  • [ 22123-14-4 ]
  • [ 1384261-71-5 ]
  • [ 1384261-99-7 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene;bis-triphenylphosphine-palladium(II) chloride; tri-tert-butyl phosphine; In N,N-dimethyl-formamide; at 150℃; for 0.166667h;microwave irradiation; Inert atmosphere; In a microwave vial 1,1-dimethylethyl (lR,4S,6R)-4-ethynyl-3-azabicyclo[4.1.0]heptane-3- carboxylate D5 (250 mg), 2-chloro-6-m ethyl -4-(trifluoromethyl)pyri dine (221 mg, 1.130 mmol), Cs2C03 (368 mg, 1.130 mmol), bis(triphenylphosphine)palladium(II) chloride (15.86 mg, 0.023 mmol), tri-t-butylphosphine (10.96 mu, 0.045 mmol) and DBU (14 mu, 0.093 mmol) were dissolved in DMF (4 ml). The vial was sealed under nitrogen and the mixture was irradiated for 10 minutes at 150 C.The reaction mixture was cooled to 23 C, diluted with EtOAc (30 ml) and filtered through a Celite pad. The filtrate was washed with brine (3 x 20 ml) and the combined aqueous layers were back extracted with EtOAc (2 x 5 ml). Organic layers were dried (Na2S04), filtered and evaporated.The brown oil obtained was purified by column chromatography (SNAP KP-Sil 50g; eluted with Cy/EtOAc 3CV from 100% Cy to 90/10, 5CV 90/10).Evaporated fractions gave the title compound D44 as yellow oil (128 mg).UPLC (IPQC): rt = 1.43 minutes, peak observed: 381 (M+l) C20H23F3N2O2 requires: 380.1H NMR (400 MHz, CHLOROFORM-^ delta ppm 0.03 (br. s., 1 H) 0.75 (td, 1 H) 0.97 - 1.20 (m, 2 H) 1.42 - 1.54 (m, 9 H) 1.93 (br. s., 1 H) 2.27 (br. s., 1 H) 2.60 - 2.71 (m, 3 H) 3.74(br. s., 1 H) 4.01 (d, 1 H) 4.94-5.32 (br. s., 1 H) 7.30 - 7.34 (m, 1 H) 7.47 (s, 1 H)
  • 17
  • 6-(trifluoromethyl)-3-pyridinylboronic acid [ No CAS ]
  • [ 22123-14-4 ]
  • [ 1401163-91-4 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 120℃; for 0.166667h;Microwave irradiation; Example 118A 6-methyl-4,6'-bis(trifluoromethyl)-2,3'-bipyridine A 20 mL microwave vial was charged with 6-(trifluoromethyl)pyridin-3-ylboronic acid (644 mg, 3.37 mmol), <strong>[22123-14-4]2-chloro-6-methyl-4-(trifluoromethyl)pyridine</strong> (600 mg, 3.07 mmol), bis(triphenylphosphine)palladium(II) chloride (108 mg, 0.153 mmol), and K2CO3 (848 mg, 6.14 mmol), followed by the addition of DME (9.0 mL), water (3.86 mL) and ethanol (2.57 mL). The mixture was heated in the microwave at 120 C. for 10 minutes. The combined reaction mixtures were added 200 mL EtOAc, and filtered through a celite pad. The filtrate was washed with 200 mL water and 200 mL brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on a Grace Reveleris 80 g column, eluted with 0-40% EtOAc in Hexanes (35 mL/min) to provide the title compound (2.858 g, 9.33 mmol, 101% yield) as a yellow solid. MS (ESI+) m/z 307.1 (M+H); 1H NMR (300 MHz, DMSO-d6) delta 9.51 (d, J=2.1, 1H), 8.82 (ddd, J=8.4, 2.2, 0.5, 1H), 8.36 (s, 1H), 8.06 (dd, J=8.4, 0.5, 1H), 7.78 (s, 1H), 2.70 (s, 3H).
  • 18
  • 6-(trifluoromethyl)-3-pyridinylboronic acid [ No CAS ]
  • [ 22123-14-4 ]
  • [ 1401163-92-5 ]
  • 19
  • [ 22123-14-4 ]
  • C21H25F4N3O [ No CAS ]
  • 20
  • [ 22123-14-4 ]
  • C24H31F4N3O [ No CAS ]
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